Synthesis of Diheterocyclic Compounds Based on Triazolyl Methoxy Phenylquinazolines via a One-Pot Four-Component-Click Reaction

被引:35
作者
Dabiri, Minoo [1 ]
Salehi, Peyman [2 ]
Bahramnejad, Mahboobeh [1 ]
Sherafat, Fatemeh [1 ]
机构
[1] Shahid Beheshti Univ, GC, Fac Sci, Dept Chem, Tehran 1983963113, Iran
[2] Shahid Beheshti Univ, GC, Dept Phytochem Med Plants & Drugs, Res Inst, Tehran 1983963113, Iran
来源
JOURNAL OF COMBINATORIAL CHEMISTRY | 2010年 / 12卷 / 05期
关键词
CLICK CHEMISTRY; MULTICOMPONENT; INHIBITORS; DISCOVERY; DNA;
D O I
10.1021/cc100043z
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A facile and highly efficient method for one-pot four-component synthesis of triazolyl methoxy phenylquinazolines is described. A mixture of aromatic propargylated aldehydes, different azides, 2-aminobenzophenone derivatives, and ammonium acetate were condensed in the presence of catalytic amounts of acidic ionic liquid, 1-methylimidazolium trifluoroacetate, ([Hmim]TFA), and Cu(OAc)(2)/sodium ascorbate to afford the corresponding products in excellent yields. This methodology is highly efficient for structurally diverse azides.
引用
收藏
页码:638 / 642
页数:5
相关论文
共 25 条
[1]   Tandem multicomponent/click reactions:: synthesis of functionalized oxazoles and tetrazoles from acyl cyanides [J].
Clemencon, Isabelle F. ;
Ganem, Bruce .
TETRAHEDRON, 2007, 63 (35) :8665-8669
[2]   Novel and efficient one-pot tandem synthesis of 2-styryl-substituted 4(3H)-quinazolinones [J].
Dabiri, Minoo ;
Baghbanzadeh, Mostafa ;
Delbari, Akram Sadat .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (05) :700-703
[3]   A new and efficient one-pot procedure for the synthesis of 2-styrylquinolines [J].
Dabiri, Minoo ;
Salehi, Peyman ;
Baghbanzadeh, Mostafa ;
Nikcheh, Maryam Shakouri .
TETRAHEDRON LETTERS, 2008, 49 (37) :5366-5368
[4]   Ammonium salt catalyzed multicomponent transformation: simple route to functionalized spirochromenes and spiroacridines [J].
Dabiri, Minoo ;
Bahramnejad, Mahboobeh ;
Baghbanzadeh, Mostafa .
TETRAHEDRON, 2009, 65 (45) :9443-9447
[5]   Water-Accelerated Selective Synthesis of 1,2-Disubstituted Benzimidazoles at Room Temperature Catalyzed by Brnsted Acidic Ionic Liquid [J].
Dabiri, Minoo ;
Salehi, Peyman ;
Baghbanzadeh, Mostafa ;
Shakouri Nikcheh, Maryam .
SYNTHETIC COMMUNICATIONS, 2008, 38 (23) :4272-4281
[6]   Click chemistry -: What's in a name?: Triazole synthesis and beyond [J].
Gil, Maria Victoria ;
Arevalo, Maria Jose ;
Lopez, Oscar .
SYNTHESIS-STUTTGART, 2007, 11 (11) :1589-1620
[7]   γ-Methyl-substituted-γ-butyrolactones:: solid-phase synthesis employing a cyclisation-cleavage strategy [J].
Gouault, N ;
Cupif, JF ;
Sauleau, A ;
David, M .
TETRAHEDRON LETTERS, 2000, 41 (38) :7293-7297
[8]   Targeting the α-folate receptor with cyclopenta[g]quinazoline-based inhibitors of thymidylate synthase [J].
Henderson, Elisa A. ;
Bavetsias, Vassillos ;
Theti, Davinder S. ;
Wilson, Stuart C. ;
Clauss, Rainer ;
Jackman, Ann L. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (14) :5020-5042
[9]   Novel chemical class of pUL97 protein kinase-specific inhibitors with strong anticytomegaloviral activity [J].
Herget, T ;
Freitag, M ;
Morbitzer, M ;
Kupfer, R ;
Stamminger, T ;
Marschall, M .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2004, 48 (11) :4154-4162
[10]   Combining Biginelli multicomponent and click chemistry: Generation of 6-(1,2,3-triazol-1-yl)-dihydropyrimidone libraries [J].
Khanetskyy, B ;
Dallinger, D ;
Kappe, CO .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (06) :884-892